WO1992009637A1 - Procede de production d'un derive de cyclodextrine et polymere contenant de la cyclodextrine immobilisee - Google Patents

Procede de production d'un derive de cyclodextrine et polymere contenant de la cyclodextrine immobilisee Download PDF

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Publication number
WO1992009637A1
WO1992009637A1 PCT/JP1991/001011 JP9101011W WO9209637A1 WO 1992009637 A1 WO1992009637 A1 WO 1992009637A1 JP 9101011 W JP9101011 W JP 9101011W WO 9209637 A1 WO9209637 A1 WO 9209637A1
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Prior art keywords
cyclodextrin
derivative
producing
reaction
compound
Prior art date
Application number
PCT/JP1991/001011
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English (en)
Japanese (ja)
Inventor
Masanobu Yoshinaga
Original Assignee
Toppan Printing Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Toppan Printing Co., Ltd. filed Critical Toppan Printing Co., Ltd.
Priority to EP91913121A priority Critical patent/EP0513358B1/fr
Priority to KR1019920701297A priority patent/KR927003647A/ko
Priority to DE69127810T priority patent/DE69127810T2/de
Publication of WO1992009637A1 publication Critical patent/WO1992009637A1/fr
Priority to US08/237,725 priority patent/US5608015A/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof

Definitions

  • the present invention relates to a method for producing a cyclodextrin derivative and a method for producing a cyclodextrin-immobilized polymer, and more particularly, to a basic monomer unit.
  • a method for producing a cyclodextrin derivative capable of immobilizing cyclodextrin of one unit without fail and a method of producing a cyclodextrin-immobilized polymer. It relates to a manufacturing method.
  • Cyclodextrin has more than 6 units of glucose ⁇ -1,
  • cyclodextrin ring is hydrophobic, and the size of this ring is determined by the amount of glucose unit. Utilizes selective inclusion, such as fillers for chromatographic separation, catalysts, or masking of off-flavors, off-flavors of foods, retention of volatile substances, solubilization of hardly soluble substances, etc. Used.
  • JP-B-55-27083, JP-B-55-41643, and JP-B-56-15806 describe a method for producing a polystyrene-based polymer having a cyclodextrin derivative. According to this method, one unit of cyclodextrin derivative is always immobilized on the styrene monomer, but in the polymer reaction, the reactivity is low and the immobilization amount is sufficient.
  • JP-A-55-75402, JP-A-63-314201, and the like disclose a polymer reaction of cyclodextrin at a glycidyl group or at a position where the epoxy ring is opened.
  • an object of the present invention is to provide a method for producing a CD derivative which can be used as a raw material of a polymer for immobilizing a CD and in which a protecting group is introduced into only one of hydroxyl groups of the CD. It is to be.
  • the object of the present invention is to prepare a monomer such as an acid halide of an ⁇ , / 3 unsaturated acid or a monomer such as an ⁇ , 3 unsaturated acid having an isocyanate group at a terminal. It is intended to provide a method for producing a cyclodextrin-immobilized polymer, which immobilizes a cyclodextrin derivative of the present invention and exhibits high reactivity even in its polymer reaction. And.
  • the above-mentioned object of the present invention is to provide cyclodextrin with a carboxylic acid halide, an acid anhydride or a compound represented by the following formula: [1] to [5] or a compound represented by the following formulas [6] and [7], or by reacting the cyclodextrin methyl
  • a protecting group such as alcohol amide, alcohol alcohol or glycolic acid, or the following formula [ 8] to [10] to introduce a protecting group into only one of the primary hydroxyl groups of cyclodextrin
  • the method for producing cyclodextrin derivatives which is characterized by an unsaturated halide or an acid halide monomer of its derivative, or an / S unsaturated compound having an isocyanate group at a terminal,
  • a method for producing a cyclodextrin derivatives which is characterized by an unsaturated halide or an acid halide monomer of its derivative, or an / S unsaturated compound having an iso
  • a cyclodextrin derivative having a protecting group introduced into only one of the primary hydroxyl groups of cyclodextrin is used, and 1 unit of cyclodextrin or a derivative thereof is immobilized on the monomer. It has been found that this can be achieved by a method for producing a cyclodextrin-immobilized polymer that specializes in the formation of a polymer.
  • R and R ′ each represent an isopropyl group, a phenyl group or a benzyl group, and X represents C £, Br or I.
  • Si—CH 3 or C-Bu-t (t-Bu; CH 3 —C-I) represents CH 3 H 3 CH 3, and R ′ represents a hydrogen atom or one OCH 3 .
  • n an integer of 2 to L 0, preferably 2 to 5.
  • R represents a hydrogen atom or one OCH 3.
  • cyclodextrin (hereinafter abbreviated as CD) is reacted with a halogenated carboxylic acid.
  • the halogenated carboxylic acid used here is used.
  • a carboxylic acid chloride is preferable, and specifically, aryloxycarboxylic acid chloride, P-nitrovinylcarboxylic acid chloride, benzyloxycarboxylic acid chloride, benzylthiocarboxylic acid chloride is preferable.
  • trichloroethoxycarboxylic acid chloride, tribromoethoxycarboxylic acid chloride and the like are used.
  • a method for selectively oxidizing one of the methylol groups of CD for example, reacting CD with paratoluenesulfonyl chloride
  • a method is used in which one of the tyrol groups is tosylated and then reacted with potassium iodide or the like to form a halide.
  • the alcohol is reacted with the CD, and the hydroxyl group is protected by a protecting group, and the alcohol, alcohol, and glycolic acid are ethanol.
  • various compounds having a longer methylene chain for example, propanolamine, butanolamine, merilecaptopropyl alcohol, etc.
  • various compounds in which the above-mentioned compounds such as hydroxyshetylethanolamine and the like are further extended as ethylene chains are also included.
  • protecting groups for protecting these hydroxyl groups include, for example,
  • the protecting group portion is converted to a reactive group such as a hydroxyl group.
  • a monohydroxy CD derivative is obtained which can be supported without cross-linking to the polymer, and which is easy to quantify since only one reacts with the polymer unit at the same time. be able to.
  • Etherification or esterification is, for example, the reaction of a CD derivative having a protective group introduced with a halogenated alkynole such as methyl iodide, an acid chloride such as benzoyl chloride, or an acid anhydride such as acetic anhydride. It is done more.
  • a halogenated alkynole such as methyl iodide
  • an acid chloride such as benzoyl chloride
  • an acid anhydride such as acetic anhydride
  • any one of CD, ⁇ -CD, and arc CD can be used.
  • monohydroxy CD is an acid halide monomer of a ⁇ -unsaturated acid or a derivative thereof or a monomer having an isocyanate group at the terminal, or a monomer of an unsaturated acid or a derivative thereof. And immobilize 1 unit of the CD derivative on the monomer.
  • Acrylic acid, methacrylic acid and the like are used as the unsaturated acid, and these monomers are used as monohydroxy-CD as described above.
  • the polymer can be polymerized or copolymerized with methyl methacrylate to produce a polymer having CD immobilized thereon.
  • a method is also possible in which a copolymer containing the acid halide is synthesized in advance and then subjected to a polymer reaction with monohydroxy CD to immobilize the CD.
  • a synthesis reaction of a CD derivative used for producing the CD-immobilized polymer of the present invention will be described.
  • R ′ represents a group such as CH 3 —C—.
  • n 6 (a C D), 7 — C D) or 8 (a-C D))
  • the compound [3] is dissolved in DMF, NaH is added at 0 to 5 ° C under a nitrogen stream, and the mixture is stirred at that temperature for 2 hours, shielded from light, added with methyl iodide, and then added at room temperature. For one day and night. After completion of the reaction, the mixture is filtered, and DMF is distilled off under reduced pressure. Add a small amount of ethanol to the residue and reprecipitate from a large amount of water. The precipitate is thoroughly washed with water and dried under reduced pressure to obtain compound [4]. (Yield: 40%)
  • Identification can be performed by NMR spectrum, mass spectrum, and elemental analysis.
  • n 6 ( ⁇ -CD), 7 (3-CD) or 8 ( ⁇ -CD).
  • the obtained mono 3 — CD derivative tetrahydrobiranilated compound (or tetrahydrodiothiopyranylated compound) [10] is dissolved in dehydrated methanol, and 4 to 5 M methanol alcohol is dissolved. (In methanol) was added dropwise at room temperature. After the completion of the dropwise addition, the reaction is carried out at room temperature for 24 hours. After the completion of the reaction, the precipitate is filtered. The cation-exchange resin was added to the filtrate, and the mixture was stirred at room temperature for 2 hours. After completion, the mixture was filtered to remove the resin. The filtrate is concentrated under reduced pressure, Water is added to the residue, and clo-mouth extraction is performed. The black form layer is concentrated under reduced pressure, and the residue is separated by silica gel chromatography. ⁇ Purification is performed to obtain the target product, monohydroxyl 3-CD derivative (D).
  • the obtained mono / 3-CD derivative tetrahydrobiranilide (or tetrahydropyranylanilide) [26] is dissolved in ethanol, and the solution is dissolved in ethanol. Add 2M NaOH aqueous solution and stir at room temperature for 2 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, and the residue was extracted with a cross-linked form-monohydrate system. The chloroform layer is concentrated under reduced pressure, and the residue is separated and purified by silica gel chromatography to obtain the monohydroxy / 3-CD derivative (L). obtain.
  • the precipitate is collected and dried under reduced pressure.
  • the precipitate obtained is dissolved in DMF, NaH is added under a nitrogen stream, and the mixture is reacted at room temperature for 3 hours.Methyl iodide is added at 0 ° C, and the hydroxyl group is added. Methylation of Let's do it. The methylation is performed in a dark room for 24 hours. After the completion of the reaction, the mixture is filtered, the filtrate is distilled off under reduced pressure, and the residue is extracted with water-Z-chloroform. The mouth layer is concentrated under reduced pressure, ethanol is added to the crude product to dissolve it, and then reprecipitation is carried out from a large amount of water. After filtering the resulting precipitate, the filtrate is purified by silica gel chromatography to obtain mono-6-0-trimethyl-peru0-methyl-CD. : 75%) o
  • silylating agents such as trimethylsilyl norechloride, triethylsilyl norechloride or t-butyldimethyl norechloride, are primary hydroxyl groups. Further, a plurality of secondary hydroxyl groups may react, but the above-mentioned silylating agent involves steric hindrance or reacts under the above conditions, and only one functional group is introduced into the primary hydroxyl group.
  • compound [30] is obtained in the same manner as in synthesis (a) or (mouth) of compound [24] in reaction example (10).
  • Mono) S—CD derivative for example, acetylated compound [32] is dissolved in dioxane and reacted by passing ammonia gas at room temperature. Start. After the start, bring the system to 50 ° C and react for 6 hours. After completion of the reaction, the reaction mixture is left to cool, dioxane is distilled off under reduced pressure, and the residue is extracted with formaldehyde water. The mouth layer is washed with dilute hydrochloric acid and water, dried, concentrated under reduced pressure, and the residue is separated and purified by silica gel chromatography to obtain the desired product (0). obtain.
  • compound (P) is obtained in the same manner as in the synthesis of compound (0) in Reaction Example (13).
  • the precipitate is recrystallized from II-butanol / ethanol Z water and purified (yield: 60%). Then benzyl alcohol ( " ⁇ CH 2 0 H) and the N a H is reacted in a nitrogen atmosphere in DMF, this at room temperature - CD mono Aiodi de of DMF was added, 24 followed 70 to 80 ° C Let react for hours. After completion of the reaction, DMF is distilled off under reduced pressure, and the residue is reprecipitated from a large amount of acetate.
  • the reaction is carried out in an atmosphere, and a DMF solution of -CD mono-iodide is added at room temperature, followed by a reaction at 70 to 80 ° C for 24 hours. After completion of the reaction, DMF is distilled off under reduced pressure, and the residue is reprecipitated with a large amount of acetate. Collect the precipitate and dry under reduced pressure The precipitate obtained by drying was dissolved in DMF, NaH was added under a nitrogen stream, and the mixture was reacted at room temperature for 3 hours.Methyl iodide was added at 0 ° C to hydroxylate the hydroxyl group. No. The methylation is performed in a dark room for 24 hours.
  • the mixture is filtered, the filtrate is distilled off under reduced pressure, and the residue is extracted with a water Z-cloth form system.
  • the chloroform layer is concentrated under reduced pressure, ethanol is added to the crude product to dissolve it, and then reprecipitation from a large amount of water.
  • the filtrate is purified by column chromatography to obtain /?-CD (mono-6-trityl-loop 0-methyl ⁇ -CD) (yield : 75%).
  • mono-lumetyl / 3-CD ((a) derivative mono--6-allyl-per- ⁇ -methyl ⁇ -CD) is dissolved in DMS 0, and the mixture is dissolved at 50 ° C using t-Bu OK. Stir for 1 hour and then at room temperature for 24 hours to cause isomerization. Thereafter, an aqueous solution of H g C £ 2 in the presence of H g O is added to the system. Then, stir at room temperature for 6 hours. After completion, filter and concentrate the solution under reduced pressure. To the residue was added black form, and the mixture was filtered again. The black form was distilled off under reduced pressure, and the residue was separated by silica gel chromatography to obtain monohydroxylethyl methyl. CD mono-6 -hydroxyethy 1-per-0-methyl ⁇ -CD) is obtained (yield: (a) ⁇ 25%, (b) ⁇ 35 ° / o).
  • Identification can be performed by NMR spectrum, mass spectrum, and elemental analysis.
  • CD derivatives can be prepared according to the above method.
  • the synthesis reaction of the above-mentioned CD-immobilized polymer is specifically carried out as follows.
  • the obtained monomer (I) and methyl methacrylate in dioxane, and azobisisobutyronitrile (AIBN) as an initiator, are mixed at 80 ° C for 8 hours. Perform polymerization. After completion of the reaction, re-precipitate it by adding it to a large amount of methanol. The precipitate is thoroughly washed with methanol and dried to obtain the CD polymer (II).
  • Polymer (V) is obtained by copolymerizing methyl methacrylate and methacryloyrussocyanate in butyl acetate using AIBN as an initiator under a nitrogen stream at 80 ° C for 5 hours. . Allowed to cool to room temperature Later, cooling the system to 0 to 5 e C to the al, compounds dissolved in butyl acetate (A) (R:. CH I) is added dropwise. After dropping, stir at 0 to 5 for 5 hours. Next, the unreacted isocyanate group is crushed with methanol, and reprecipitation is performed with a large amount of acetate. The precipitate is washed well with acetone and dried to obtain CD polymer (VI).
  • Benzyl methyl methacrylate and methacryloyl phenol are copolymerized with AIBN as the initiator under a nitrogen stream at 80 ° C for 5 hours. Get. Then, let it cool to room temperature, add triethylamine, cool the system to 0-5 ° C, and add dropwise the monohydroxyl ⁇ -CD methylated product dissolved in benzene. After the completion of the dropwise addition, the reaction was carried out at room temperature for 6 hours. Then, the unreacted terminal group (—C—C) was replaced with diazome.
  • a CD derivative which can be used as a raw material for a CD-immobilized polymer and has a protective group introduced into only one hydroxyl group of the CD
  • the reaction between an acid halide or an isocyanate group and an alcohol is performed, the reactivity is high, and the immobilization of CD is performed well.
  • we provide a method for manufacturing a CD-immobilized polymer that is easy to quantify. can do.
  • the CD-immobilized polymer obtained as described above was used for chromatography. It is used for separating fillers, catalysts, or masking off-flavors and off-flavors in foods, retaining volatile substances, and solubilizing hardly soluble substances.

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Abstract

Procédé de production d'un polymère contenant de la cyclodextrine immobilisée. Le procédé consiste à faire réagir la cyclodextrine avec un halogénure acylique ou un anhydride acide de l'acide carboxylique, un composé répondant à l'une quelconque des formules (a), (b), (c), (d), (e), ou un autre composé; et à faire réagir le dérivé de cyclodextrine ainsi obtenu avec un monomère d'halogénure acylique d'un acide α,β-insaturé ou d'un dérivé de celui-ci, ou un monomère d'un acide α,β-insaturé à terminaison isocyanate ou d'un dérivé de celui-ci. Dans lesdites formules, X représente Cl, Br ou I. Le polymère ainsi obtenu renferme une unité à dérivé de cyclodextrine immobilisée pour chaque monomère et présente une réactivité élevée dans la réaction polymère.
PCT/JP1991/001011 1990-11-30 1991-07-29 Procede de production d'un derive de cyclodextrine et polymere contenant de la cyclodextrine immobilisee WO1992009637A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP91913121A EP0513358B1 (fr) 1990-11-30 1991-07-29 Procede de production d'un derive de cyclodextrine et polymere contenant de la cyclodextrine immobilisee
KR1019920701297A KR927003647A (ko) 1990-11-30 1991-07-29 시클로덱스트린유도체 및 시클로덱스트린 고정화 폴리머의 제조방법
DE69127810T DE69127810T2 (de) 1990-11-30 1991-07-29 Verfahren zur herstellung eines cyclodextrinderivates und polymer welches darin immobilisiertes cyclodextrin enthält
US08/237,725 US5608015A (en) 1990-11-30 1994-05-04 Processes for producing cyclodextrin derivatives and polymers containing immobilized cyclodextrin therein

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP33553190 1990-11-30
JP2/335532 1990-11-30
JP2/335531 1990-11-30
JP33553290 1990-11-30

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US (1) US5608015A (fr)
EP (1) EP0513358B1 (fr)
KR (1) KR927003647A (fr)
CA (1) CA2066633A1 (fr)
DE (1) DE69127810T2 (fr)
WO (1) WO1992009637A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5929131A (en) * 1997-01-06 1999-07-27 American Dental Association Health Foundation Polymerizable cyclodextrin derivatives
JPWO2018159791A1 (ja) * 2017-03-02 2020-01-23 国立大学法人大阪大学 ホスト基含有重合性単量体、高分子材料及びその製造方法、並びに、包接化合物及びその製造方法
US11279774B2 (en) 2019-01-03 2022-03-22 Underdog Pharmaceuticals, Inc. Cyclodextrin dimers, compositions thereof, and uses thereof

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE9300912U1 (de) * 1993-01-23 1993-04-29 Macherey, Nagel GmbH & Co. Handelsgesellschaft, 52355 Düren Trennmaterial für die Chromatographie
EP0668294B1 (fr) * 1994-02-15 1999-08-18 Novartis AG Dérivés insaturés d'hydrates de carbone, leurs polymères et leurs utilisations
TW307775B (en) * 1994-02-15 1997-06-11 Novartis Erfind Verwalt Gmbh Unsaturated carbohydrate derivatives, polymers thereof and their use
US6509323B1 (en) * 1998-07-01 2003-01-21 California Institute Of Technology Linear cyclodextrin copolymers
US7091192B1 (en) * 1998-07-01 2006-08-15 California Institute Of Technology Linear cyclodextrin copolymers
US7375096B1 (en) * 1998-12-04 2008-05-20 California Institute Of Technology Method of preparing a supramolecular complex containing a therapeutic agent and a multi-dimensional polymer network
US6613703B1 (en) 2000-04-27 2003-09-02 Kimberly-Clark Worldwide, Inc. Thermoplastic nonwoven web chemically reacted with a cyclodextrin compound
TWI321054B (en) 2000-12-19 2010-03-01 California Inst Of Techn Compositions containing inclusion complexes
US6527887B1 (en) 2002-01-18 2003-03-04 Mach I, Inc. Polymeric cyclodextrin nitrate esters
MX367615B (es) 2002-09-06 2019-08-28 Cerulean Pharma Inc Polimeros a base de ciclodextrina para el suministro de agentes terapeuticos.
EP1549269A4 (fr) * 2002-10-09 2010-10-06 Cerulean Pharma Inc Materiaux et compositions a base de cyclodextrine, et utilisations correspondantes
JP2010516625A (ja) 2007-01-24 2010-05-20 インサート セラピューティクス， インコーポレイテッド 制御された薬物送達のためのテザー基を有するポリマー−薬物コンジュゲート
KR101456526B1 (ko) * 2007-10-19 2014-11-03 에스케이씨 주식회사 사이클로덱스트린 유도체 및 이를 포함하는 저굴절률 소재
CN102781237A (zh) * 2009-11-23 2012-11-14 天蓝制药公司 用于传递治疗剂的基于环糊精的聚合物
ITTO20110873A1 (it) 2011-09-30 2013-03-31 Sea Marconi Technologies Di Vander Tumiatti S A S Uso di nanospogne funzionalizzate per la crescita, la conservazione, la protezione e la disinfezione di organismi vegetali.
US9408419B2 (en) 2012-03-23 2016-08-09 Victoria's Secret Store Brand Management, Inc. Moisturizing fabric material, use thereof in moisturizing bras, and method of manufacture
US20140094432A1 (en) 2012-10-02 2014-04-03 Cerulean Pharma Inc. Methods and systems for polymer precipitation and generation of particles
NL2019374B1 (en) 2017-07-28 2019-02-19 Academisch Ziekenhuis Leiden Kit and Method for Microarterial Imaging and Radiotherapy
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CN114750484A (zh) * 2022-05-17 2022-07-15 史秀龙 一种长效抗污面料及其制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5461289A (en) * 1977-10-24 1979-05-17 Iwao Tabuse Method of making polystyrene base polymer containing cyclodextrine derivative
JPS5513796A (en) * 1978-07-13 1980-01-30 Chinoin Gyogyszer Es Vegyeszet Cyclodextrinnpolyvinyl alcohol*polymer and process for polymerizing same in form of particles*fibers*block or film
JPS5575402A (en) * 1978-11-30 1980-06-06 Mitsubishi Chem Ind Ltd Fixing of cyclodextrin
JPS5757701A (en) * 1980-08-07 1982-04-07 Chinoin Gyogyszer Es Vegyeszet Cellulose derivative and manufacture
JPS59227906A (ja) * 1983-06-10 1984-12-21 Mitsubishi Chem Ind Ltd 固定化シクロデキストリンアミノ誘導体及びその製造法
JPS61129566A (ja) * 1984-11-28 1986-06-17 Wako Pure Chem Ind Ltd メチル化シクロデキストリン固定相及びこれを用いる液体クロマトグラフイ−
JPS63314201A (ja) * 1987-06-17 1988-12-22 Japan Organo Co Ltd シクロデキストリンの固定化方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169079A (en) * 1977-10-24 1979-09-25 Iwao Tabushi Polystyrene based polymers containing cyclodextrin derivatives, metal complexes of the same, and process for the production of the same
MY106598A (en) * 1988-08-31 1995-06-30 Australian Commercial Res & Development Ltd Compositions and methods for drug delivery and chromatography.
US5096893A (en) * 1989-04-03 1992-03-17 The United States Of America As Represented By The Department Of Health And Human Services Regioselective substitutions in cyclodextrins
US5173481A (en) * 1989-04-03 1992-12-22 The United States Of America As Represented By The Department Of Health And Human Services Preparation of specifically substituted cyclodextrins
EP0485614B1 (fr) * 1990-05-21 1997-08-13 Toppan Printing Co., Ltd. Derive de cyclodextrine
JPH0425505A (ja) * 1990-05-21 1992-01-29 Toppan Printing Co Ltd シクロデキストリンポリマー及びシクロデキストリン膜の製造方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5461289A (en) * 1977-10-24 1979-05-17 Iwao Tabuse Method of making polystyrene base polymer containing cyclodextrine derivative
JPS5513796A (en) * 1978-07-13 1980-01-30 Chinoin Gyogyszer Es Vegyeszet Cyclodextrinnpolyvinyl alcohol*polymer and process for polymerizing same in form of particles*fibers*block or film
JPS5575402A (en) * 1978-11-30 1980-06-06 Mitsubishi Chem Ind Ltd Fixing of cyclodextrin
JPS5757701A (en) * 1980-08-07 1982-04-07 Chinoin Gyogyszer Es Vegyeszet Cellulose derivative and manufacture
JPS59227906A (ja) * 1983-06-10 1984-12-21 Mitsubishi Chem Ind Ltd 固定化シクロデキストリンアミノ誘導体及びその製造法
JPS61129566A (ja) * 1984-11-28 1986-06-17 Wako Pure Chem Ind Ltd メチル化シクロデキストリン固定相及びこれを用いる液体クロマトグラフイ−
JPS63314201A (ja) * 1987-06-17 1988-12-22 Japan Organo Co Ltd シクロデキストリンの固定化方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0513358A4 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5929131A (en) * 1997-01-06 1999-07-27 American Dental Association Health Foundation Polymerizable cyclodextrin derivatives
JPWO2018159791A1 (ja) * 2017-03-02 2020-01-23 国立大学法人大阪大学 ホスト基含有重合性単量体、高分子材料及びその製造方法、並びに、包接化合物及びその製造方法
JP2021181573A (ja) * 2017-03-02 2021-11-25 国立大学法人大阪大学 ホスト基含有重合性単量体、高分子材料及びその製造方法、並びに、包接化合物及びその製造方法
US11279774B2 (en) 2019-01-03 2022-03-22 Underdog Pharmaceuticals, Inc. Cyclodextrin dimers, compositions thereof, and uses thereof

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EP0513358A1 (fr) 1992-11-19
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US5608015A (en) 1997-03-04
DE69127810D1 (de) 1997-11-06
EP0513358B1 (fr) 1997-10-01
KR927003647A (ko) 1992-12-18
DE69127810T2 (de) 1998-03-12

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